Anonymous Confessions

Over 40,790+ Anonymous Confessions Shared!

Welcome to the ultimate confession booth, Men Only!

This is the space where you can share your deepest, darkest, and most embarrassing misadventures without judgment. Have you ever found yourself in a cringe-worthy situation that you couldn’t shake off? Perhaps you got caught checking out your boss's wife, or you accidentally sent a sext to your mom instead of your girlfriend. Maybe you were the guy who couldn't hold his liquor at the office party, or you clogged the toilet at your date's house.

We understand that being a man comes with its own set of unique challenges, triumphs, and mishaps. From awkward boners at the most inconvenient times to embarrassing wardrobe malfunctions, we've been there. This is your opportunity to share your stories of masculinity in all its glory, from the hilarious to the humiliating. So go ahead, confess your secrets and release your burdens. The community is here to support (or laugh at) you bro, no matter how wild or embarrassi

- Masculine Misadventures -
Straight Male / 46

Sex With The Trainer

At my last job you had to complete a 2 week training at their regional headquarters in Atlanta. They paid for all your transportation needs and meals but the weekend in between the two weeks was on you meaning you were on your own minus the hotel. I decided against flying back that weekend and chose to stay at the hotel and maybe see a little bit of Atlanta. I met the trainer at the Hotel bar and had some nice conversation with her. She is young, short, and pretty and I loved looking at her big ass when she wrote stuff on the dry erase board. She chose to remain in Atlanta as well and hang out at the hotel all weekend. I talked her into drinks and dinner with more drinks. Fortunately it was more than she could handle and we had some yummy unprotected sex in her room. I took pictures of her while she was asleep, mostly because I've never had a woman before with tits that big or that perfect. We had mind blowing sex about 3 more times throughout the weekend and the next week of training. She loved my big dick and I couldn't get enough of her tits and ass. Well she woke me up pissed off on Monday, she'd suspected that I took pictures of her and she went through my phone and found them. I tried to explain but she threw me out of the room naked screaming and apparently filed a complaint with HR. I panicked, got a cab to the airport and flew home. My wife never found out about the incident and I'm relieved. This may sound ridiculous but that was the absolute Best ass ever and it was totally worth it. I just wished I had PW protected my phone.

0
# 64633 - by Ben
    • - Masculine Misadventures -
    Bi-Sexual Male / 61

    Best. Day. Ever.

    This happened when I was a young man, a long time ago, 25. Not yet bisexual, just chasing girls. I was never much of a ladies' man but ended up in a few nice relationships with cute sexy girls. It was the early spring of 1988. I had broken up the prior fall with a sweet girl, after a year of dating and fucking, because I had moved back into the city and was focusing on my studies. But we would talk on the phone occasionally. Let's call her Kate. After Kate and I split, I dated Lisa for a few months, real intense fun sex but nothing serious. We called it quits after a few months, a month before what I am going to describe happened. Three weeks after Lisa and I split up, I was visiting a friend out of town (two hours by train) for the weekend and met a lovely sweet girl, Donna, and we really hit it off, but only kissed and made out a little. I suggested to her that I come back the following Friday by train and visit her by myself, and she quickly said yes - as I said, we really hit it off, there was a hot attraction.

    As the week passed, I was more and more horny to visit Donna.

    On Thursday afternoon, one day before my trip, Kate telephoned me out of the blue, going on about how she missed me, and asking me to come see her for old time's sake that night. Her parents were away and she said we could stay in and make dinner and have the whole house to ourselves. Well how could I say no? So I took a bus out to Kate's and we sucked and fucked all night and into the next morning. It was so hot that it made me think I should never have broken up with her (another story for another day). When we finally finished up I convinced Kate to drive me home into the city, and arrived around 10:00 a.m. I was feeling mighty fine.

    I went outside and was sitting on my stoop with a cup of coffee when suddenly, Lisa came by on her bicycle (we lived about a mile from each other). She said she hoped she would find me home as she wanted to let me know she was moving the following week to California, to go to grad school. Then she asked me if I wanted to come over for a little goodbye. Well how could I resist. Having not even showered after Kate, I hurried over to Lisa's tiny apartment and we proceeded to fuck like rabbits for the next two hours. Because I had been cumming all night, I was able to last and last. Lisa was so exhausted when I was done with her.

    By then, I had to rush back home, grab some clothes, and catch the two hour train to meet Donna, who started blowing me in the train station parking lot in her car. We didn't stop all weekend.

    What a day!

    0
    # 64622 - by That Guy
    - Masculine Misadventures -
    Lesbian Female / 27

    A Man Took Me Over For Him, But My Girlfriend Didn't Give Up On Me

    I had a workout class in the mornings before work. A girl came every day and I had a crush on her. Her name was special, she was special. I talked to her and tried to make friends, but it was a class only thing. A woman, older than us, joined the group and she went after this girl and I caught her kissing her in the women's room. My heart exploded, I had never felt more jealous in my life, I screamed at her for moving in on my girl, but my girl was in her arms and she was being kissed and she wasn't trying to get away.

    At work that day I was upset and my supervisor, a man, came in and asked me if everything was alright. I tried to ignore him and get him to leave but he didn't. What's up, get it off your chest. I told him flat out that I liked this girl and this woman had moved in on her. He said something about knowing the feelings, once you have your sights on a girl you don't want anyone getting close to her. Then he said something like "there just isn't anything like pussy". I agreed with him. It was out so why hide it. Until he said "I want your pussy, I want to eat your pussy, I want to fuck your pussy, I don't want anyone moving in on you, male or female, as far as you are concerned that pussy is my pussy". "My pussy".

    He had gotten up to leave but turned around. "Tomorrow morning you wake up beside me, is that understood". He had my pussy, he ate my pussy, he fucked my pussy and I woke up beside him. He didn't believe he was the first one to have my pussy or that he was my first dick. He moved me that weekend into his place and set me up. Because it was the weekend he wanted sex all weekend. Sit over his face and lower my pussy down to him. Suck his dick and spread my legs around his head so he could take it all in. Suck my tits, lay back and have me lean over him and feed him tits like if he was eating gr**es. But most of all he wanted pussy.

    That Sunday, in the afternoon after we had gone out to eat, he took a magic marker and after having me shave my mound completely, wrote on me "This is my pussy" and he signed his name. A week after that he had me get a tattoo "Mike's pussy".

    I was crazy, I didn't know what was going on, he was fucking me two times a day and eating me before and after. On the following Friday after I got my tattoo with him he told me he wanted me married. I married him, or he married me, it was a small thing with a few friends, a couple of my special friends from my life with the girls. They both kissed me on the mouth in front of him, she may be your wife, but she's our girl. It all sort of became real when we flew to Denver to meet my parents. The first hint was me walking in with a diamond ring on my finger and I told them I hadn't had my period.

    I lived the life with him. My favorite friend kissed me every time she saw me, she grabbed some booby, and she shaved my pussy for him. She wanted him to know that no matter what I was hers, and she wanted me waking up with her, whether or not I was pregnant. He told me again what he had told me that day in the office, he had his sights on me forever and now that I was his pussy no one was moving in on me. But my favorite girlfriend wasn't ever going away, I needed her beside me, and I wanted to wake up beside her. Being pregnant drove me to want sex so bad with her, she shaved me, and ate me. I shaved her in return and ate her. I may have been married, but I kissed a girl.

    He put his foot down, and she ignored him. That shit was not for her. She is the one that was with me in the delivery room. He may be the father, but she was the other mother. If he didn't like it, well she was willing to get pregnant. She would close the deal, but she wasn't leaving me and she was waking up with me. Whether he was there or not didn't matter. She wasn't giving up her pussy. And that's how it is.

    She is pregnant and I guess I never realized just how big an ass you have when you're packing. Sorry.

    0
    # 64574 - by Sasha
    • - Masculine Misadventures -
    Straight Male / 36

    Trapped In Leather, My Endless Fantasy Becomes Reality

    I've always fantasized about being kept in a strait-jacket, otherwise naked, and endlessly fucked at both ends, by a pair of older, tough-guys, for weeks, months, even...

    Recently a pair of escapees from the local prison found my unlocked patio door, and carried out a very private 'home invasion' during which they found me asleep, half-way into my strait-jacket, a horrendously expensive custom-made affair, of expensive leather, lined with latex, and with an attached hood, whose drawcords could hold it tight to my face, so that the zippered opening lay right over my mouth. Well obviously they quickly completed the process, until I was utterly helpless, and after making themselves at home, for a day or so, decided to have some fun with me.

    I ended up on one guy's lap, his hard cock gradually penetrating me deep and deeper, my legs dr**ed over the fat padded arms of the old armchair, while his buddy stood in front, his cock in my mouth, via the zippered opening. One lifted me up and down, on his cock, while the other thrust in and out of my mouth. The one under me reached around and was mauling my swollen testicles, and sliding up and down my shaft, as the other pumped in and out slowly and intensely, until his ejaculation hit the back of my throat, triggering a swallow reflex. Then he withdrew, and closed the zipper tightly, and soon after that his partner exploded inside me, and lifted me off, and out of the chair. On weak shaky legs, I allowed myself to be put back to bed, and they settled down to watch some football game or another. I slept after a while.

    The armchair position has been inflicted on me several times a day, and they discuss at length just how long they can take advantage of their situation. Some serious orgasm denial drew a full confession from me, as to my seclusion and lack of friends or family, and how there was really nothing to stop them making this menage permanent.

    A year later, nothing has changed, and I crave my time in the armchair to the exclusion of all good sense and judgment, as my permanency fantasy grows more and more likely. Now totally compliant, I am allowed an hour a day, to feed myself, toiletries, exercise, and what I'm doing now....

    0
    # 46119 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 47

    After finishing my MBA I took a job for an oil company. I met a girl who worked for an accounting firm. Truthfully it never crossed my mind that she could have been a virgin, totally inexperienced when it came to sex. I was 27 and she was 23. Sex was a bit wild, a bit hard, and a bit restraining, I had to hold her down.

    Well she announced to her close friends that we were a couple, I told the same people in her dreams. Some weeks later she had an out of town conference and I decided to surprise her. I went up on my own and met her when she came out of the conference room. She was surprised, especially when she found out I was staying with her. That night much against her will I poked her good in the ass and fucked her balls to the wall. Butt fucked did it, now there was only one thought on her mind. Get married.

    Well it took a good while before we got married, two more years. She kept up the act, no sex. But sex happened, including more anal when she was in her period, lots of oral, she loved sucking on a dick. And she told me she had heard about it the day she shaved her pussy and sat on the kitchen table and told me she was giving me clams for dinner. She invented, because I was caught off guard, when, where, how. Sex was not held back, she liked being brought around, she got wetter than hell when she was taken by force.

    It is now twenty years of this, she comes up with stuff, I will say we have given up on anal, got bored with it, but giving me a naked ass crack flash going up the stairs of the theater or giving me a quick blowjob in the car are very much on the table.

    0
    # 46018 - by Anonymous
    • - Masculine Misadventures -
    Bi-Sexual Male / 48

    Sometimes it is nice to reminisce, especially about something that really made your engine run hot. I had to go to Gabon. At the time I was working for a shipping company as a Maintenance Engineer, to go observe an inspection of the main power generators and give it the pass or fail. I arrived out of Paris and checked into the hotel. Along with me a man that had sat in the isle seat across from me also checked in, a French man.

    We said hello and took our bags upstairs, we had rooms next door. He asked if I was going down for a drink so I agreed and we met in the bar by the pool. There were two topless women, he said they were flight attendants and he knew them. He also told me that we would be wasting our time. We talked, introduced ourselves really, he was with a law firm and after a couple of drinks he suggested we get something to eat.

    At dinner there was a lot of small talk, and talk about politics and the economy and his comments about the US economy and to be truthful he was pretty well informed. After dinner we walked out onto the beach and he offered me a cigar with I turned down. He touched my arm and then my shoulder and said that he found me interesting. Back at the hotel on the elevator he invited me to his room for a nightcap, he said he had some very good Cognac.

    The Cognac was good, he took off his shoes and socks and the next thing I know he is taking off his pants and shirt, she slips his shorts off and comes over to me and asks me if I want to join him, his cock under his undershirt already at somewhere near hard. There is a minute when you don't know what to do, his cock is in my face, his naked legs beside me, he has his hand on the back of my head and I realize I am being pulled forward. His cock is now on my mouth, no words just his cock against my lips.

    You have to let yourself go sometimes and I opened my mouth slowly and soon his cock head was in my mouth and then his cock was in my mouth, my tongue running all over it, finding his pee hole and I am sucking on his cock. I am not repulsed, I am really quite into it. Maybe not something I would ever do but here I was sucking on his cock. He took off his undershirt, went to the bed and took the covers off and laid back on the bed and asked me to come join him.

    He was hard, his cock was hard in his hand and he offered it to me again. I got my shoes off and my pants and my shirt and then my shorts and undershirt, and with nothing other than my watch and my socks I got on the bed and went back to sucking his cock. My cock got hard and then softened up and got hard again and softened up, depending on whether I was thinking about my cock or just sucking on his.

    After a few minutes he mentioned that I needed to move up the bed and he took my cock in his hand and I took his cock in mine and we started kissing, making out like teenagers. His hand on my cock felt amazing, and his cock in my hand felt dangerous. We kissed for quite a while, he bent down and sucked my cock for a bit and went to the bathroom and came back with a small bottle and he told me to settle down, and I let him rub the liquid all over my asshole. That I was going to get fucked wasn't in question, my question was how, how did I place myself.

    A bit more kissing and his cock slamming against my thigh and he pushed me onto my side and I felt his cock exploring my asshole, by then I was quite ready for him to do it, he pushed me onto my stomach and gave me a pillow to put under me and with his hot hairy chest on my back he slipped his cock into me. I was amazed as to how easy it went in, and how good it felt. I relaxed and he did all the work. Soon he was off and my asshole was cold again. It felt funny, a strange feeling.

    We lay on the bed for a while, he asked me if I wanted to spend the night or go back to my room. By then I was ready to go back to my room, I got dressed and we said goodnight and I went back to lay on my bed and just relive what had happened. It was a long time before that when I last jerked off with my hand, that night I jerked off, it felt good and I went to sleep.

    It has not been easy finding someone to play around with like that. Mostly I have hooked up via an internet forum, always when I am traveling overseas. I don't know when my next trip will be, but I am looking forward to it. I miss the company and hopefully I can make arrangements with a like minded soul.

    1
    # 45938 - by Anonymous
    100 of 40,785 Confessions Displayed.

    © Copyright 2025 Anonymous Confessions | All Rights Reserved.